Diisopropylethylamine → (3,5-Dimethylisoxazol-4-yl)(piperazin-1-yl)methanone

A solution of 1-tert-butyloxycarbonyl-piperazine (4.581 mmol, 0.9 eq) and diisopropylethylamine (5.09 mmol, 1.0 eq) in methylene chloride (5 mL) was added to a 40 mL vial. 3,5-Dimethyl-isoxazole-4-carbonyl chloride (5.09 mmol, 1.0 eq) was added to the vial and the reaction was shaken overnight at room temperature. When the reaction was complete, it was diluted with methylene chloride (5 mL) and washed with 4 mL of 1N HCl followed by 4 mL of 10% potassium carbonate. The organic layer was concentrated in vacuo. The crude residue was dissolved in 5 mL of dioxane and 5 mL of 4M hydrochloric acid in dioxane. The reaction mixture was shaken overnight at room temperature then centrifuged. The supernatant was removed and the remaining solid was shaken with hexane then centrifuged. The supernatant was removed, and the solids were collected and dried in vacuo to give (3,5-dimethyl-isoxazol-4-yl)-piperazin-1-yl-methanone. LR-MS: 210.2 [(M+H)+]

1. washwashed with 4 mL of 1N HCl
2. concentrationThe organic layer was concentrated in vacuo
3. dissolutionThe crude residue was dissolved in 5 mL of dioxane
4. stirringThe reaction mixture was shaken overnight at room temperature
5. customThe supernatant was removed
6. stirringthe remaining solid was shaken with hexane
7. customThe supernatant was removed
8. customthe solids were collected
9. customdried in vacuo

ORD record

ord-89c1494203c74e8aa5dae1e32fa1f9fb

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07964724B2